4381-25-3Relevant academic research and scientific papers
Iron-Catalyzed Amination of Sulfides and Sulfoxides with Azides in Photochemical Continuous Flow Synthesis
Lebel, Hélène,Piras, Henri,Borduy, Marie
, p. 1109 - 1112 (2016)
A photochemical (UVA) continuous flow process for the amination of thioethers and sulfoxides was performed with trichloroethoxysulfonyl azide in the presence of catalytic iron(III) acetylacetonate. Aromatic and aliphatic sulfilimines and sulfoximines were produced in high yields and short reaction times. The reaction with chiral sulfoxides was stereospecific, producing enantioenriched sulfoximines in excellent yields.
Metal-free imination of sulfoxides and sulfides
Cho, Gae Young,Bolm, Carsten
, p. 8007 - 8008 (2005)
Using a nitrogen transfer agent obtained in situ by mixing of NsNH 2 and PhI(OAc)2, various N-nosyl sulfoximines and N-nosyl sulfilimines have been prepared under metal-free conditions starting from the corresponding sulfoxides and s
Synthesis and bioactivity of new phosphorylated R,R′-substituted sulfoximines
Bellozas, Monica,De Licastro, Susana Arnstein
, p. 1369 - 1376 (2005)
R,R′-disubstituted sulfoximines were phosphorylated with O,O-diethylchloro phosphate and phosphorothionate to obtain new organophosphorus compounds. After purification they were characterized by GC-MS and 1H-NMR. The toxicity of the synthesized
Electrochemical Oxidative Syntheses of NH-Sulfoximines, NH-Sulfonimidamides and Dibenzothiazines via Anodically Generated Hypervalent Iodine Intermediates
Kong, Xianqiang,Lin, Long,Chen, Xiaohui,Chen, Yiyi,Wang, Wei,Xu, Bo
, p. 3277 - 3282 (2021/07/26)
Herein, we report a general method for the synthesis of NH-sulfoximines and NH-sulfonimidamides through direct electrochemical oxidative catalysis involving an iodoarene(I)/iodoarene(III) redox couple. In addition, dibenzothiazines can be synthesized from [1,1′-biaryl]-2-sulfides under standard conditions. Notably, only a catalytic amount of iodoarene is required for the generation in situ of an active hypervalent iodine catalyst, which avoids the need for an excess of a hypervalent iodine reagent relative to conventional approaches. Moreover, this protocol features broad substrate scope and wide functional group tolerance, delivering the target compounds with good-to-excellent yields even for a scale of more than 10 g.
Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes
Amri, Nasser,Wirth, Thomas
, p. 15961 - 15972 (2021/07/20)
An efficient electrochemical flow process for the selective oxidation of sulfides to sulfoxides and sulfones and of sulfoxides toN-cyanosulfoximines has been developed. In total, 69 examples of sulfoxides, sulfones, andN-cyanosulfoximines have been synthesized in good to excellent yields and with high current efficiencies. The synthesis was assisted and facilitated through a supporting electrolyte-free, fully automated electrochemical protocol that highlights the advantages of flow electrolysis.
Chiral Dibenzopentalene-Based Conjugated Nanohoops through Stereoselective Synthesis
Hermann, Mathias,Wassy, Daniel,Kohn, Julia,Seitz, Philipp,Betschart, Martin U.,Grimme, Stefan,Esser, Birgit
, p. 10680 - 10689 (2021/04/02)
Conjugated nanohoops allow to investigate the effect of radial conjugation and bending on the involved π-systems. They can possess unexpected optoelectronic properties and their radially oriented π-system makes them attractive for host–guest chemistry. Be
Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents
Alharbi, Haifa,Elsherbini, Mohamed,Karam, Fatemah,Osi, Arnaud,Wirth, Thomas
, (2021/06/21)
Chiral hypervalent iodine reagents are active players in modern stereoselective organic synthesis. Structurally diverse chiral hypervalent iodine reagents have been synthesised and extensively studied, but hypervalent iodine reagents containing chiral sul
Synthesis and Configurational Assignment of Vinyl Sulfoximines and Sulfonimidamides
Craven, Gregory B.,Briggs, Edward L.,Zammit, Charlotte M.,McDermott, Alexander,Greed, Stephanie,Affron, Dominic P.,Leinfellner, Charlotte,Cudmore, Hannah R.,Tweedy, Ruth R.,Luisi, Renzo,Bull, James A.,Armstrong, Alan
, p. 7403 - 7424 (2021/06/25)
Vinyl sulfones and sulfonamides are valued for their use as electrophilic warheads in covalent protein inhibitors. Conversely, the S(VI) aza-isosteres thereof, vinyl sulfoximines and sulfonimidamides, are far less studied and have yet to be applied to the field of protein bioconjugation. Herein, we report a range of different synthetic methodologies for constructing vinyl sulfoximine and vinyl sulfonimidamide architectures that allows access to new areas of electrophilic chemical space. We demonstrate how late-stage functionalization can be applied to these motifs to incorporate alkyne tags, generating fully functionalized probes for future chemical biology applications. Finally, we establish a workflow for determining the absolute configuration of enantioenriched vinyl sulfoximines and sulfonimidamides by comparing experimentally and computationally determined electronic circular dichroism spectra, enabling access to configurationally assigned enantiomeric pairs by separation.
Novel NH - sulfoxide imine compound and synthesis method thereof
-
Paragraph 0027-0030, (2021/09/21)
The invention discloses a novel NH - sulfoxide imine compound and a synthesis method thereof, the novel NH - sulfoxide imine compound widens the kind of NH - sulfoxide imine compounds and lays a foundation for synthesis of a NH - sulfoxide imine skeleton
Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis
Liu, Dong,Liu, Zhao-Ran,Ma, Cong,Jiao, Ke-Jin,Sun, Bing,Wei, Lei,Lefranc, Julien,Herbert, Simon,Mei, Tian-Sheng
supporting information, p. 9444 - 9449 (2021/03/29)
A novel strategy for the N-arylation of NH-sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a NiII species is crucial to promote the reductive elimination of a C?N bond from the resulting NiIII species at room temperature.
